Sodium Iodide → 4-(2-Oxazolo[4,5-c]pyridin-2-ylvinyl)-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

NaI (2 mg) was added to a solution of 4-(2-chloro-2-oxazolo[4,5-c]pyridin-2-ylethyl)-piperidine-1-carboxylic acid tert-butyl ester (Example 22, 18 mg, 49 μmol) in anhydrous pyridine (1 mL). The mixture was heated under microwave irradiation for 10 min at 150° C., before being concentrated in vacuo. The residue was taken up in EtOAc (20 mL), then the EtOAc solution was washed with a mixture of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (1:1, 2×8 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (EtOAc-IH, 17:3) yielded 4-(2-oxazolo[4,5-c]pyridin-2-ylvinyl)-piperidine-1-carboxylic acid tert-butyl ester as a 1:1 mixture of (E)- and (Z)-isomers: m/z (ES+)=330.1 [M+H]+. A solution of this compound (10 mg, 30 μmol) in EtOH (1 mL) was stirred with Pd (10% on C, 1 mg) under a H2 atmosphere for 4 h. The mixture was filtered through celite, washing with MeOH. The combined filtrates were concentrated under reduced pressure to afford the title compound: RT=2.89 min; m/z (ES+)=332.2 [M+H]+.

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